685-24-5

Basic information

• Product Name: 1,1,1,4,4,4-HEXAFLUOROBUTANE-2,3-DIONE
• Synonyms: 1,1,1,4,4,4-HEXAFLUOROBUTANE-2,3-DIONE;PERFLUORODIACETYL;1,1,1,4,4,4-Hexafluoro-2,3-butadienone
• CAS NO: 685-24-5
• Molecular Formula: C₄F₆O₂
• Molecular Weight: 194.03
• EINECS: 1533716-785-6
• Mol File: 685-24-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 20°C
• Appearance: /
• Density: 1.6
• Vapor Pressure: 2280mmHg at 25°C
• Refractive Index: 1.283
• CAS DataBase Reference: 1,1,1,4,4,4-HEXAFLUOROBUTANE-2,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,1,4,4,4-HEXAFLUOROBUTANE-2,3-DIONE(685-24-5)
• EPA Substance Registry System: 1,1,1,4,4,4-HEXAFLUOROBUTANE-2,3-DIONE(685-24-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 685-24-5(Hazardous Substances Data)

Usage

General Description

1,1,1,4,4,4-HEXAFLUOROBUTANE-2,3-DIONE, also known as hexafluoroacetone, is a colorless liquid with a pungent odor. It is a powerful oxidizing agent and is highly reactive with a wide range of organic and inorganic compounds. It is used in the synthesis of fluorinated organic compounds and as a solvent for metal complexes. Hexafluoroacetone is also used as a chemical intermediate in the production of pharmaceuticals, agrochemicals, and specialty chemicals. However, it is highly toxic and poses health risks if inhaled, ingested, or absorbed through the skin. It is also a potential environmental hazard and should be handled with extreme caution.

InChI:InChI=1/C4F6O2/c5-3(6,7)1(11)2(12)4(8,9)10

Upstream product

• 76293-22-6 cis-2,3-difluoro-5,6-bis(trifluoromethyl)-2,3-dihydro-p-dioxin 
• 201230-82-2 carbon monoxide 
• 692-50-2 hexafluoro-2-butyne 
• 360-89-4 octafluoro-2-butene 

Downstream Products

• 62754-83-0 5-Phenoxy-2,3-bis-trifluormethyl-1,4,6,10-tetraoxa-5-phosphaspiro<4.5>dec-2-en 
• 67348-13-4 2-diethylamino-2-fluoro-2-phenyl-4,5-bis-trifluoromethyl-2λ⁵-[1,3,2]dioxaphosphole 
• 67348-14-5 2-diethylamino-2-fluoro-2-p-tolyl-4,5-bis-trifluoromethyl-2λ⁵-[1,3,2]dioxaphosphole 
• 53799-42-1 2-Phenoxy-2,2-o-phenylendioxy-4,5-bis-(trifluormethyl)-2,2-dihydro-1,3,2-dioxaphospholen 
• 98170-49-1 2,2-bis(tetrahydrofurfuryloxy)-2-phenyl-4,5-bis(trifluoromethyl)-1,3,2-dioxaphosphol-4-ene 
• 484058-58-4 4',5'-bis(trifluoromethyl)-4-oxo-2-phenyl-2λ⁵-spiro[benzo[e][1,3,2]dioxaphosphinine-2,2'-[1,3,2]dioxaphosphole] 
• 82052-84-4 2-p-fluorophenoxy-2,2-di-(2-furyl)-4,5-bistrifluoromethyl-1,3,2-dioxaphosphole 
• 129918-33-8 8-Phenyl-2,3-bis-trifluoromethyl-5-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-1,4,6,10-tetraoxa-5λ⁵-phospha-spiro[4.5]dec-2-ene 
• 107210-65-1 6-benzoyl-2,3-bis(trifluoromethyl)quinoxaline 
• 67348-10-1 2,2-difluoro-2-phenyl-4,5-bis-trifluoromethyl-2λ⁵-[1,3,2]dioxaphosphole 
• 53799-44-3 2,2,2-Tris-p-tolyloxy-4,5-bis-trifluoromethyl-2λ⁵-[1,3,2]dioxaphosphole 

Relevant articles and documents

Photolysis of hexafluoro-2-butyne/ozone mixtures in cryogenic matrices

Matrix studies on the photolytic reaction between ozone and hexafluoro-2-butyne have been performed at 11 K in argon and nitrogen matrices. The matrices were photolyzed with 640 and 642 nm light from a laser source, and with 254 nm light from a Hg arc lamp. The final products of the reaction are perfluorobutanedione and bis(trifluoromethyl)ketene. An intermediate species was also observed. It has been identified as perfluoroacetylmethylmethylene, a ketocarbene. The ketocarbene was also trapped as trifluoromethyl trifluoroacetylketene, a ketoketene, when the matrix was doped with CO. Photolysis of the ketocarbene with 427 nm light results in the direct formation of the ketene. The ketocarbene and ketene form as a result of O atom addition to the butyne, whereas the butanedione appears to be predominantly produced by a reaction between the ketocarbene and O2. Product distribution was found to depend greatly on both matrix material and ozone concentration. This is the first direct evidence of a ketocarbene as an intermediate in the O atom addition to an alkyne.

Heterocyclic Polyfluoro-compounds. Part 33. Competing 1,2- and 1,4-Photochemical Addition of Hexafluorobiacetyl to 1,2-Difluoroethylene

Photochemical addition of hexafluorobiacetyl (λ > 300 nm) to either cis- or trans-1,2-difluoroethylene yields mainly cis-2,3-difluoro-5,6-bis(trifluoromethyl)-2,3-dihydro-p-dioxin (53 - 57percent), and the corresponding trans-dioxin (12percent) by 1,4-addition, together with r-2-trifluoromethyl-2-trifluoroacetyl-t-3,t-4-difluoro-oxetan (7 - 8percent) and the corresponding t-3,c-4- (7 - 8percent) and c-3,t-4-oxetans (6 - 7percent) by 1,2-addition.The cis-dioxin yields both cis- and trans-1,2-difluoroethylene upon pyrolysis, and with aluminium trichloride undergoes isomerisation to the trans-dioxin, and non-stereospecific exchange of one or both ring fluorines by chlorine atoms.